Disease relevance of DIAMINOPIMELIC ACID

• Strains of Escherichia coli K12 have been constructed as safer hosts for use in recombinant DNA research, These strains are unable to survive passage through the intestinal tracts of rats because of a constellation of mutations conferring bile sensitivity and requirements for diaminopimelic acid and thymine [1].
• Diaminopimelic acid-containing peptidoglycan, produced by Gram-negative bacteria, is recognized by two receptors, PGRP-LC and PGRP-LE, and activates a homolog of transcription factor NF-kappaB through the Imd signaling pathway [2].
• Diaminopimelic acid was absent in the Legionnaires' disease bacterium peptidoglycan [3].
• L,L-diaminopimelate aminotransferase, a trans-kingdom enzyme shared by Chlamydia and plants for synthesis of diaminopimelate/lysine [4].
• Proteins required for the synthesis of peptidoglycan and incorporation of diaminopimelic acid into cell walls have been solubilized from Bacillus megaterium toluene-treated cells [5].

High impact information on DIAMINOPIMELIC ACID

• When a chromosomal or plasmid-borne copy of ampD was present, the amount of pentapeptide-containing muropeptides in the cell wall increased upon addition of the cell wall constituent diaminopimelic acid to the growth medium [6].
• Here we report that Gram-negative diaminopimelic acid-type peptidoglycan is the most potent inducer of the Imd pathway and that the Toll pathway is predominantly activated by Gram-positive lysine-type peptidoglycan [7].
• Enzyme digestion of CW, in particular by lysozyme, was found to reduce a PG characteristic component (diaminopimelic acid) without altering CW antitumor activity [8].
• The diaminopimelic acid (DAP)-type peptidoglycan potently activates imd-dependent induction of antibacterial peptides [9].
• Diaminopimelic acid, also formed by this enzymatic pathway, is an integral component of bacterial cell walls, thus making ASADH an attractive target for the development of new antibiotics [10].

Chemical compound and disease context of DIAMINOPIMELIC ACID

• The peptidoglycan of Thermotoga maritima, an extremely thermophilic eubacterium, was shown to contain no diaminopimelic acid and approximate amounts of both enantiomers of lysine (Huber, R., Langworthy, T. A., König, H., Thomm, M., Woese, C. R., Sleytr, U. B., and Stetter, K. O. (1986) Arch. Microbiol. 144, 324-333) [11].
• Crystal structure of UDP-N-acetylmuramoyl-L-alanyl-D-glutamate: meso-diaminopimelate ligase from Escherichia coli [12].
• The Mycobacterium tuberculosis lysA gene encodes the enzyme meso-diaminopimelate decarboxylase (DAPDC), a pyridoxal-5'-phosphate (PLP)-dependent enzyme [13].
• One strain of Fusobacterium, F. mortiferum VPI 0473 contained both lanthionine and diaminopimelic acid in about equal proportions [14].
• Antibiotic TA inhibited incorporation of diaminopimelic acid and uridine diphosphate-N-acetylglucosamine into Escherichia coli cell walls without altering the ratio of cross-linked to uncross-linked peptidoglycan [15].

Biological context of DIAMINOPIMELIC ACID

• Nucleotide sequence of the meso-diaminopimelate D-dehydrogenase gene from Corynebacterium glutamicum [16].
• This biocatalyst was the result of three rounds of mutagenesis and screening performed on the enzyme meso-diaminopimelate d-dehydrogenase [17].
• The longest open reading frame potentially encodes a peptide of 431 amino acids and exhibits similarity to other eukaryotic ODCs, prokaryotic and eukaryotic arginine decarboxylases (ADCs), prokaryotic meso-diaminopimelate decarboxylases and the product of the tabA gene of Pseudomonas syringae cv. tabaci [18].
• Stable expression of PspA was achieved by the use of the balanced-lethal vector-host system, which employs an asd deletion in the host chromosome to impose an obligate requirement for diaminopimelic acid [19].
• The first one encodes a 118-residue polypeptide that is not required for diaminopimelic acid biosynthesis, as judged by the wild-type phenotype of a strain in which this gene was disrupted [20].

Anatomical context of DIAMINOPIMELIC ACID

• An enzyme activity, responsible for the attachment of diaminopimelic acid (DAP) to bdelloplast wall peptidoglycan, was studied in an in vitro, cell-free system [21].
• Diaminopimelic acid in feces indicated that differences in taurine degradation rate among groups was associated with differences in bacterial numbers in feces [22].
• Lack of lysogenic induction in "diaminopimelic acid spheroplasts" [23].
• In strains with an increased flow of precursors to D,L-diaminopimelate, however, the inactivation of the dehydrogenase pathway resulted in a reduced formation of lysine, with concomitant accumulation of N-succinyl-diaminopimelate in the cytosol up to a concentration of 25 mM [24].
• In this work we used the haemocyte-like mbn-2 cell line to investigate how expression of the antimicrobial peptide diptericin is affected after a high dose bacterial challenge with diaminopimelic acid (DAP)-peptidoglycan Gram-positive and Gram-negative bacteria [25].

Associations of DIAMINOPIMELIC ACID with other chemical compounds

• We generated a diaminopimelic acid (DAP) auxotroph (AA400) of L. pneumophila by disruption of the aspartate-beta-semialdehyde (asd) gene [26].
• N-Acetyl-D-alanyl-L-isoglutamine, diaminopimelic acid, and L-rhamnose caused a significant dose-dependent inhibition of C1q binding to bacteria, suggesting that these molecules, at least, are involved in the attachment of C1q to L. monocytogenes cell wall [27].
• The presence of 2-keto-3-deoxyoctonate, muramic acid, and diaminopimelic acid suggests that the preparation is highly enriched in cell wall [28].
• The revertants exhibited the normal lytic response when treated with D-cycloserine and beta-lactams or when deprived of diaminopimelic acid at 42 degrees C. The basis for the autolysis-defective phenotype of these mutants could not be determined [29].
• Increased bacterial fermentation and excretion as well as increased bacterial folate production in the presence of added DF and UFDM were demonstrated by increased volatile fatty acid content in cecal and fecal samples (P < 0.000001) and increased diaminopimelic acid, muramic acid and folate in feces (P < 0.00001) [30].

Gene context of DIAMINOPIMELIC ACID

• This mutant accumulated large amounts of LL-diaminopimelate, confirming the blockage in the step catalyzed by the dapF product, but did not require meso-diaminopimelate for growth [31].
• The predicted amino acid sequence of ADC contains a region of six amino acid residues found in two bacterial diaminopimelic acid decarboxylases and three eucaryotic ornithine decarboxylases [32].
• In contrast, complementation of E. coli dapD8, presumably lacking L-delta 1-tetrahydrodipicolinate synthetase (dapD), led us to clone a diaminopimelate-lysine anabolic gene of C. glutamicum which does not exist in E. coli: meso-diaminopimelate dehydrogenase [33].
• This mutant showed the lysA- or lysR- genotype since it could not grow on the minimal plate which contained diaminopimelic acid [34].
• We show here that this is not the case and that expression of LacZ from the dapA promoter (PdapA) increases in response to diaminopimelic acid limitation in E. coli K-12 [35].

Analytical, diagnostic and therapeutic context of DIAMINOPIMELIC ACID

• A number of biochemical markers, including diaminopimelic acid content, monosaccharide composition, mycolic acid, and glycolipid distribution, were applied to their characterization, and two-dimensional gel electrophoresis was used to map the component proteins [36].
• Using a rapid thin-layer chromatography method, the isomer of diaminopimelic acid and sugar in the whole cell hydrolysate were studied [37].
• Gram-negative cell walls were also measured by using two-dimensional gas chromatography/electron-capture analysis of diaminopimelic acid originating from the peptidoglycan [38].
• Cloning and sequence analysis of the meso-diaminopimelate decarboxylase gene from Bacillus methanolicus MGA3 and comparison to other decarboxylase genes [39].
• High-resolution autoradiography of thin sections of Escherichia coli cells whose murein was pulse-labeled with [3H]diaminopimelic acid after a period of diaminopimelic acid deprivation indicated that elongation of the murein sacculus occurs by a multisite (diffuse) process [40].

References